Felix organizes a "dare night" to test the limits of his new classmates. While out playing the game, Lucas meets a mysterious new girl, Anna. Peyton tearfully confesses to the church that she recently tried cocaine and Keith is caught off guard when a beautiful woman comes to the shop and begins flirting with him. Meanwhile, Karen goes on a date with Andy, her younger professor.

The opening of Karen's club "TRIC" brings together the people of Tree Hill. Lucas and Felix come to blows over Anna. After Chris quits his gig the night of the club opening, Haley must face her fear of performing to save the night for Peyton. Although Mouth tends to Brooke while she is drunk, Felix sneaks in and attempts to take the credit. Keith and Jules realize their relationship has reached a new level, while Dan deliberately tells Karen that Deb slept with Keith.